


Baby Did a Bad Bad Thing

by Gamermom



Series: To Woo(e) a Hunter [3]
Category: Supernatural
Genre: Crobby - Freeform, Demons Are Assholes, F/F, F/M, One Night Stands, Porn With Plot, Sad Porn
Language: English
Status: Completed
Published: 2018-07-21
Updated: 2018-07-21
Packaged: 2019-06-13 21:49:20
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 2,336
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15374067
Author URL: https://archiveofourown.org/users/Gamermom/pseuds/Gamermom
Summary: After a fantastic night with Sam and Dean at bar, Bobby has a surprise visitor in his motel room. Our favorite curmugion gets some must needed loving, metaphors get mixed and Crowley gives some truly  terrible excuses.





	Baby Did a Bad Bad Thing

**Author's Note:**

> This takes place directly after One Bourbon, One Whisky, One Beer. Caroline is the awesome bartender that Bobby spent all night chatting up. This is mostly porn with plot at the very end. Please heed the tags and see the end notes for spoilers.

Bobby had just finished laying salt lines around the dingy motel room when there was a knock at the door. He had already stripped down to his undershirt and socks, but his jeans were still on, so he figured he was dressed enough. Grabbing his pistol to complete the ensemble, he peered though the peephole. Blinking he slips the gun into the waistband of he jeans and opens the door.

“Caroline,” he gasps at the pretty bartender from the hipster bar he had just spent the most pleasant evening he had in a while. “What are you doing here?”

The pretty brunette held up a six back of beer and let her long, purple coat fall open. Bobby swallowed hard as all her creamy skin was revealed. Her perky breasts stood proud, her nipples hardening along with Bobby’s cock. His eyes trailed down, passed her flat stomach and over to her perfect bush, neatly trimmed.

            “I would have thought it was obvious. But if you don’t want company I can go,” she said as she turned to go.

            “No!” cried Bobby as he followed her out of his doorway. The streetlight illuminated Caroline’s form and made her hair glow. She grinned naughty at the older man.

            “Getting mixed signals here handsome. I got all dressed up like a **wolf in cheap clothing** and now you don’t seem so interested.”

            “Oh, I am very interested,” Bobby replied and to prove it he leaned down and kissed her red lips. Caroline opened her mouth and let deep it. She reached up and wrapped her arms around his neck, the six-pack resting on his back. Bobby slid his hands down and cupped her round ass. Caroline lifted her self up and wrapped her bare feet around his waist. The old hunter dug his fingers in to the soft mounds of her ass and pressed her body tight against him. Caroline arched her back so that she was taller than Bobby and used that leverage to deepen the kiss. Bobby stepped back into the room and shut the door with his foot. He pressed Caroline up against the wall and kept kissing her as one hand reached up to fondle her perky nipples.

            When they finally break for air, Caroline grins up at her new lover. Her lipstick is smeared, and her lips are swollen with beard burn. She lets the six pack fall to the ground and keeps her legs wrapped around Bobby’s waist. She plucks his battered trucker hat off and puts it jaunty on her head before reaching down between their bodies and undoes his belt, button and fly.

Bobby can’t seem to break eye contact with the enchanting siren. He wants to ask what changed, why she wants him now when she made her intentions so very clear in the bar. It’s not just the abrupt change in mind either. Women don’t usually throw themselves at him like this. Okay, women never throw themselves at him. Suddenly all doubt and paranoia fled from Bobby’s head as an elegant hand slid his hard cock into a tight, sheath of liquid heat.

“FUCK!” he eloquently cries out. Caroline just laughs, which taunts Bobby into jackhammering into her. His jeans pool to the floor, with a thud from the pistol. As his thrusts become harder and wilder, Caroline stops laughing and starts gasping. She moans as Bobby leans down and sucks her nipple into his mouth. His fingers are still digging into her ass cheeks and one hand makes for the center. Wetness had dripped from her pussy and down to her ass. Bobby traces her puckered little hole and then presses a finger in. Caroline arches her back and screams, her head banging against the wall. She wraps her legs tighter around Bobby and rides him like a bull named Larry.

“Don’t stop, please don’t stop,” she begged. “Please baby, fuck me, pound me. Oh FUCK I am so close. Please don’t stop. Oh yes! Just like that. Oh Baby yes, slid that finger in. Oh I like this, Baby, I love this. Show me what a beast you are Bobby Singer!” she growls out as she cums, hard. A few more strokes and Bobby cumming too.

The hunter pants for a few moments holding the bartender to the wall still before lifting her one more time and walking over to the bed. Caroline unwraps her legs and bounces onto the bed. Bobby holds up a finger, “wait.”

He disappears into the bathroom only to return a minute later with two cups of water and a wet rag. He hands Caroline a glass and proceeds to clean between her legs.

“Balls. I didn’t use a condom.”

“Don’t worry baby, I got it covered.”

Bobby nods and lays down next to his lover. She is so lovely in the dim light. Caroline rolls over and starts kissing his neck and collarbone. “I love how very manly you are luv. Strong, capable, hairy, it is all rather appealing.” She continues her kissing down his torso and rubs her face on his spent cock.

“Oh sweetheart, I am not a young man. It will be a while before I am ready to be ridden again.”

Caroline just gives a throaty laugh. “No worries love, do you mind if I play down here?”

Bobby just smiles down at her, she is still wearing his cap, and cups her face. “Not at all Caroline.”

She returns to her nuzzling of he soft cock and darts her pretty pink tongue out to lick his balls. Bobby gives a yelp when she tries to suck one into her mouth, they are still tender. Caroline grabs each of his knees and spreads his legs wide. Bobby tilts his hips up for easier access and nearly shoots off the bed when he feels a wet tongue on his asshole. Caroline doesn’t even pop her head up just digs her fingers into his thighs as laughs as she devours his asshole. Bobby’s brain starts to melt as her tongue pushes past his puckered start and into his body. Nips of teeth, her hands fondling her balls, her nose pressed into this taint, it is all too much and his cock starts to rise from the dead.

Caroline pulls out his ass and starts kissing and licking her way up towards his cock. Her index finger starts to play with his hole and with little effort she presses it in. Bobby just moans, ever since that night with Crowley he has pleasured himself more than once with something up his ass. Then, like everything else this night, Caroline gives no warning as she swallows his dick whole. Her face is pressed against his greying pubes. Bobby knocks his cap off her head as he rushs to run his fingers through her hair and thrust his hips forward into her wet mouth. Caroline continued to thrust her finger deeper into his ass as Bobby fucks her face.

“Oh, baby I am not going to last you doing this,” he moaned. Caroline just smiled as she chokes on his cock. She ran her tongue around the head of his cock and grips the base with her free hand, before plunging deep again.

“I am going to cum, pull off baby,” Bobby warns, like the gentleman he is. But Caroline keeps working, giving an amazing blow job until Bobby loses it and cums with a cry. The sexy bartender just swallows it down with an euthanasic slurp.

They lay side by side, panting, their bodies glistening for a few moments before Bobby makes an effort to return the favor.

“No, luv just rest.”

Bobby sighs but listens. He pulls Caroline close to his side instead and kisses her forehead. “That was amazing,” he praises.

“I am glad you liked”, she responds while tracing her finger across his chest. “For a minute there I thought you and Crowley might be an item.”

“Ha, no. He and I have history, but we are **diabolically opposed**.”

“Don’t you mean diametrically opposed?”

“Not for that that mother fucker. He is evil.”

“Oh, I thought you two were friends. Or at least had good sex.”

“I could never be friends with what he is. And yeah, we did have sex once, but it is not something I am looking forward two repeating.”

Caroline looks up at her lover and smiled wide, too wide. All her teeth were showing, and her eyes gleamed with malice until they turned red.

“But luv you just told me how much you enjoyed this little tryst.”

Bobby tried to throw Crowley off of him but the demon had his pinned down.

“What did you do! What did you do you fucking bastard!” Bobby cries out in rage. “Get out of her!” he demanded.

“Oh, relax princess, the pretty bartender is just fine. I mean she is crying and begging me to let her go, but she is unharmed and I will get out as soon as I am done having fun.”

Bobby paled. “Exorcizamus te, omnis immundus spiritus omnis satanica potestas, omnis incursion infernalis adversarii, omnis legio, omnis congregatio et secta diabolica.”

            Crowley slaps Bobby, but lets him up. The hunter scrambles to get his boxers and jeans back on.

            “I mean it Crowley get out of her right now,” he all but sobs. “What is wrong with you?”

            “Don’t blame me my mother tried to kill me, but you have already met Rowena. Will you just relax, this is just a bit of fun.”

“FUN! FUN! You have terrified this poor girl and made a _rapist_ out of me. I couldn’t hate you more in this moment if I tried. Get out of her NOW!”

The smirk fell from Caroline’s face. “Rapist? No Bobby, you didn’t know.”

“I don’t want to talk to you about this! I fucked a girl who didn’t want to. Who was screaming and crying and begging me to stop. I knew something was up. Calling me ‘luv’ saying you were wearing cheap clothing, it was so clear. I carried you over the salt lines, I knew she was acting weird, but I thought with my dick. I am surely guilty, and I surely blame you.”

“Well.. I had not considered that possibility,” Crowley responds in a soft voice. He then raises her hand and snaps. Bobby howls in desperation as both the demon and the bartender disappear. He quickly finishes getting dressed, grabs his weapons of choice and walks outside. For a moment he looks down to the bar and then back up the row of doors. He turns away from the bar and runs to Sam and Dean’s door. He pounds loudly and after a moment a sleepy looking Sam opens the door.

“Bobby what’s wrong?” Sam asks as Dean appears behind his brother.

“Crowley possessed Caroline to play some stupid game and then he disappeared with her. We need to find him and get her free.”

“The bartender?” Dean asked as he grabbed his and Sam’s weapons.

“Yeah. He came to my room wearing her. I didn’t notice. When I confronted him he snapped out.” The three men stepped out into the night air. In the distance the sun’s early light was beginning to peak up.

“There is still a car in front of the bar. Let’s try there first,” suggested Sam. The other two followed him across the parking lot and to the bar. They didn’t bother trying the handle, Dean just kicked the door in. There in the middle of the room stood a dapper as always Crowley, with a crying woman at his feet. She was wearing the same clothes as had been tending bar. As soon as she saw who was entering coming to rescue her she staggered up and ran to Bobby.

“Please, please help me,” she begged.

“I have already let you go pet, you don’t need to be rescued. If I wanted you dead, you would be roasting in hell right now. I was bored, this was just a bit of fun.” Crowley looked at the pain and anger on Bobby’s face, the fighting stance of both Sam and Dean and the weeping woman and knew there was no way to fix this tonight. He snapped his fingers.

“Is he gone,” Caroline asked in a timid voice. The feisty bartender from earlier was gone, replaced by woman struggling to understand what was happening and hold herself together.

“Yeah he is gone. Don’t worry. But first I need you to drink this, to make sure you are okay.” With that Bobby poured holy water from his flask onto her. Caroline didn’t drink, and the water washed over her face. Since she wasn’t burning the hunters figured she was clean.

“Caroline, right?” Sam asked, “Everything is going to be okay. The demon that was possessing you is gone, you don’t have any trace of it left. You are going to be fine.”

“Will someone please explain to me how this happened and what I need to do know. I don’t know what to do now. I am so cold and I just don’t know what to do.”

This time Dean tries to comfort her. “Yeah, how about we go to the dinner across the street and get you some coffee. We can talk and answer all your questions.”

 Caroline nods her head in agreement and presses her body against Bobby. “Caroline,” he starts.

“Please don’t. Please I don’t have it in me to take care of you. I heard what you said. I am not in a place to pass judgement, agree or not. All I know is I need to feel safe. It is a biological need like breathing and I think you are the only person who is going to make me feel safe right now. So yes, coffee and answers.”

Bobby shucks off his flannel and wraps it around her. Together the four of them head to diner as the dawn officially breaks the night sky.

**Author's Note:**

> Crowley possessed Caroline and had sex with Bobby while wearing her meat suit. Caroline was very much raped and Bobby feels like he did it. Crowley was honestly just messing with Bobby and wanted to show him how good sex with him could be. He was trying to convince Bobby to be with him, but being a demon he completely messed it up, again.  
> Ah man, this was hard for me to write. I really appreciate feedback even if you just want to yell at me. I would also like to know if you want to see more Caroline espeically as she becomes Hannah or if you are done with her and want to focus on the Crobby?


End file.
